Wetting, detergent, and emulsifying agents



J Patented Dec. 2, 1941- FICE.

warms, na'rnncm, mp nmsrrrmc scams I Heinrich Bertscli, Che'irznits,Germany, assignor,

b nieanc Delaware No Drawing.

Y Corporation, Wilmin to American Hyalsol gton, Dei., a corporation ofApplication July 11, 1934,

Serial N0. 734,697

11 Claims.

This invention relates to soap-like products and more particularlyrefers to the manufacture of soaps, detergents, wetting, emulsifying andstabilizing agents and the like, and to improvements in treatmentliquids for use in the textile, leather, and other industries whereinsoap or soap-like products have heretofore been used or;

are capable of use.

Water-soluble sulfuric esters produced by the action of sulfuric acid onfatty materials, including both fatty acids and esters of fatty acids,containing double linkages and/or hydroxyl groups, are widely employedas wetting, cleansing and dispersing agents in the textile and relatedindustries. Thus a sulfuric acid ester of hydroxy stearic acid may beproduced by treating oleic acid with sulfuric acid; and a sulfuric acidester of a dihydroxy stearic acid may be obtained by the treatment ofricinoleic acid with sulfuric acid. These agents were not satisfactory,since the sulfated fatty materials heretofore available containedcarboxyl groups, either free or combined, and in consequence werecapable of forming insoluble alkaline earth salts. For instance, thedimcultly soluble lime salts formed when these esters were added to hardwater produced deleterious effects in the textile industry byprecipitating from the solution and adhering to the textile materials.Such insoluble salts cannot be completely removed from the textilematerials and impart a harsh, unpleasant feel thereto. Furthermore,fatty acids are quite susceptible to rancidity upon aging and fiberstreated therewith are liable to acquire and retain a disagreeable odor.

It is an object of this invention to produce new soap-like materialshaving exceptionally satisfactory wetting, cleansing, stabilizing,dispersing and foaming properties. A further object is to producedetergents which may be substituted for or used in admixture with priorart detergents. A still further object is to obtain detergents, wettingand emulsifying agents which may be used in hard or acid water withoutthe formation of deleterious constituents. A still further object is toproduce superior dispersing agents. A still further object is to producecompounds heretofore unknown which are particularly adapted for use inthe numerous processes wherein soap or soap-like products have been usedin the past. Additional objects will become apparent from aconsideration of the following description.

In accordance with the preferred embodiment of the present invention,the aforementioned defects as well as numerous other defects are inlarge measure avoided if, instead of fatty acids or the esters of theseacids, the corresponding alcohols (which may be obtained therefrom byreplacement of the carboxyl group whether free or combined with theCHzOI-I group) are treated with sulfuric acid or with other sulfating orsulfonating agents. Commercial fats are in general essentially mixedglycerides of the various higher fatty acids, and the higher alcoholsobtainable therefrom are mixtures of alcohols of the general formulaCxHr-CHiOH. These mixtures consist predominantly of normal primaryalcohols having ten or more carbon atoms per molecule, corresponding innumber of carbon atoms to the fatty acids, free or combined, containedin the natural fats and fatty oils and the other commercially availablefatty materials from which they are derived. I have found that productssoluble in water and valuable for use as wetting, cleansing,stabilizing, dispersing and foaming agents can be obtained by treatingsuch alcohols with sulfuric acid or with other sulfating or sulfonatingagents. These alcohols may for convenience be referred to collectivelyas normal primary alcohols having more than eight carbon atoms to themolecule.

Thus this invention contemplates the conversion of the free or combinedfatty acids of fatty materials, 1. e. animal and vegetable fats andoils, and manufactured derivatives such as oleic acid or ethyl oleate,into the corresponding alcohols, and the treatment of these alcoholswith a sulfating or sulfonating agent such as sulfuric acid. Usually itis also advisable to neutralize the reaction product with an inorganicor an organic base, for example sodium hydroxide, ammonia, pyridine ortriethanolamine to form a watersoluble soap-like salt.

The precise nature of the method selected to convert the fatty materialto the alcohol may be varied. For instance, a well known method is thatof Bouveault and Blanc, in accordance with which an alkyl ester of afatty acid, e. g. an ethyl oleate, is reduced by sodium or other alkalimetal and a lower aliphatic alcohol such as butyl alcohol, or theimproved method described in my application for Letters Patent SerialNo. 472,764 may be used. Numerous processes are known for preparing thealkyl esters from fats and fatty acids and are contemplated herein.

The Bouveault and Blane process is of general application for thepreparation of both unsaturated and saturated alcohols. For instance, bythis process oleyl alcohol (C17H33CH20H) may be prepared from esters ofoleic acid (C-rvHasCOOH). An octodecyl alcohol (CnHas-CHzOH) may beformed from esters of stearic acid (CrzHas-COOH).

Mixed saturated and unsaturated alcohols result when the unfractionatedesters of the fatty acids of most natural fats, for example, tallow, arereduced according to the Bouveault and Blane process.

A very satisfactory method for preparing predominantly saturatedalcohols is catalytic hydrogenation of esters under high pressure, asdescribed in the application for U. S. Letters Patent of WilhelmNormann, Serial No. 510,326, filed January 21, 1931, and assigned to theassignee of the present application. This method may be applied directlyto the conversion of the natural glycerides, such as coconut or palmkernel oil, to primary alcohols for use in accordance with the presentinvention. I

Fatty alcohols obtained from the sources described may next be treatedwith a sulfating agent having water-binding properties. Ordinarilyconcentrated sulfuric acid may be used, or stronger reagents such asanhydrous sulfuric acid, chlorsulfonic acid, or fuming sulfuric acid.The principal reaction occurring is the formation of sulfuric esters,frequently called alkyl sulfuric acids, forinstance, as follows:

In the case of an unsaturated alcohol, some addition of sulfuric acid atthe double bond may also occur, so that complete reaction of sulfuricacid with oleyl alcohol might be according to the equation:

CH3. (CH2) 7CH=CH.(CH2) 7CH2OH+2H2SO4= H2O+CH3.(CHz) 7.CH2.CH.OSO3H.

(CH2) 1CH2.0SO3H sulfuric ester of 1,9-octodecandiol Unless a highertemperature is required to melt the alcohol I prefer to effect sulfationin the cold within the range of ordinary room temperature or lower, down,to about C. However, higher and lower temperatures can be used, and myinvention is not restricted to a particular range of temperature ofsulfation.

Under almost any practical conditions of sulfation, there may be formedat least traces of sulfonic acids, the proportion of which may beincreased by choice of sulfating medium and other conditions ofreaction, for instance, by high reaction temperatures and by the use ofhighly concentrated energetically acting reagents such as fumingsulfuric acid. While these are not my preferred reaction conditions, itshould be understood that the sulfation products made in accordance withthe present invention are not purely esters, but may contain alsoappreciable amounts of sulfonic acids or 'sulfonates. For convenience,the products resulting from the treatment with sulfuric acid or otheragents such as those hereinbefore mentioned will be referred togenerically as sulfuric reaction products.

One method of sulfating which is of fairly general application todifferent alcohol mixtures is to treat the alcohol just above itsmelting point with Hill-110% of the theoretical quantity ofchlorsulfonic acid required according to the equation:

The acid reaction products obtained as described above are preferablycarefully neutralized, for instance, with sodium hydroxide.Neutralization should ordinarily be carried out at relatively lowtemperatures, preferably in a vessel fitted with a means for cooling.The resulting alcohol salts such as sodium lauryl sulfate may beseparated from inorganic components such as sodium sulfate and sodiumchloride by known methods, for instance, by dissolving in ethyl alcohol,decanting or filtering, and evaporating off the solvent. With or withoutthis purification, the products obtained are in general readily solublein water, possess marked wetting, cleansing, stabilizing, dispersing andfoaming properties, and may be employed for manifold purposes whereinsoap or soap-like substances were heretofore used. For use in soft, hardor acid water they are pronouncedly superior to soap or the soap-likesubstances of the prior art.

The sulfated products of oleyl alcohol are particularly resistant tohardness and are highly suitable for use in the textile and relatedindustries. Probably due to the unsaturated nature of the alcohol fromwhich these esters are derived they possess properties which make themwell adapted for use alone or in admixture with saturated alcohols orderivatives of saturated alcohols. I

A high resistance to the action of hard water is shown by the sulfatedproducts of lauryl alcohol, which is the principal constituent of themixed alcohols obtained by reduction of coconut, palm kernel and similaroils, or by reduction of the alkyl esters or the free fatty acids ofthese oils. Sulfated alcohols of this class have remarkable cleansing,collecting and foaming properties, and are valuable as soap substitutes,espe cially for use in hard water.

The sulfuric reaction products derived from lauryl alcohol, especiallythe esters and salts thereof, are also found to be particularlyeffective in the textile industry. Thus when starting from the fattyalcohols made from free fatty acids of the coconut oil or palm seed oilaccording to known processes, for instance, by esterifying the fattyacids of the same with lower aliphatic alcohols and reducing the mixtureof esters by means of sodium in the presence of an alcohol, it isadvantageous to remove by distillation portions of the reductionproducts and thereby increase the proportion of lauryl alcohol in themixture to be sulfonated. Such a mixture may contain. higher and/orlower homologues of lauryl alcohol depending upon the object in view. Itshould be understood, however, that the presence of the sulfuricderivatives of lower and/or higher alcohols, such as of decyl, myristyland stearyl alcohols with the lauryl alcohol derivatives does notmaterially decrease the efficiency of the final product.

Numerous higher alcohols may be produced and converted into wetting andcleansing agents, substantially according to the procedures describedabove, for instance the following:

Alcohols obtained by catalytic hydrogenation of the free fatty acids ofcoconut oil and comprising mainly lauryl alcohol, myristyl alcohol,cetyl alcohol and stearyl alcohol or the single alcohols separated fromeach other by fractional distillation, or crystallization.

Alcohols obtained by catalytic hydrogenation of palm kernel oil or ofthe free fatty acids of palm kernel oil comprising similar constituentsalthough in somewhat difierent proportions as the alcohols obtained fromcoconut oil.

Alcohols obtained by saponification of spermaceti, sperm oil, beeswaxand distillation according to Axelrad and Hochstadter (U. S. A. Patent1,290,870).

Additional sources of alcohols according to the above or relatedprocesses are montan wax, carnauba wax, lard oil, sperm train oil,docylin train oil, ocotilla. wax and various other oils and waxes offish, animal or vegetable origin.

The following examples are given to illustrate the manner in which theprocess may be carried out:

Example 1 100 kgs. of a mixture of fatty alcohols mainly consisting oflauryl alcohol, and obtained from coconut oil by esterification of thefatty acids with ethyl alcohol, reduction of the ethyl ester,distillation of the product of the reduction and collection of theflrst'5060% of the distillate, are heated to melting temperature about30 C. and treated at this temperature with 50 kgs. of ohlorsulfonicacid.

The foregoing reaction may be represented by the following formula:

100 kgs. of pure lauryl alcohol wouldrequire for best results a higherproportion of chlorsulfonic acid, about 60 kgs.

Example 2 100 kgs. of the same mixture of fatty alcohols is sulfonatedwith 70 kgs. of fuming sulfuric acid at the temperature of 150 C.

The products of the reaction are directly neutralized by means of sodalye and separated by known methods from inorganic components such assodium sulfate or sodium chloride.

Example 3 100 kgs. of a mixture of fatty alcohols obtained by thecatalytic reduction of spermaceti with hydrogen, using a coppercatalyst, a temperature between 300-350 C. and a pressure of 150-200atmospheres until the acid number has wholly disappeared, are sulfonatedat a temperature of 35 C. with 60 kgs. of ohlorsulfonic acid. Theproduct is poured in 200 kgs. of ice water and. is then neutralized bymeans of a potassium hydroxide solution. There results a white pastereadily soluble in water.

The reactions occurring can be illustrated by the following equations:CH3.(CH2) 14.CH2OOC.(CH2) 14.CH3+2H2= 2CH3.(CH2) 14.CH2OH CH3. (CH2)14.CH2OH+C1SO3H= CH3(CH2) 14.CH2O-SO:H+HC1 Example 4 100 kgs. of oleicalcohol are sulfated at 25 C. with 80 kgs. of concentrated sulfuricacid. The mixture is poured into 150 kgs. of ice water and isneutralized by means of piperidine.

The sulfation reactions may be illustrated by the following equations:

Example 5 100 kgs. of a mixture of unsaturated and saturated fattyalcohols were obtained by reduction of coconut oil by means of an alkalimetal and butyl alcohol, adding water, separating the resulting wateryalkali hydroxide solution and removing the butyl alcohol bydistillation. The.

resulting alcohols were treated with kgs. of ohlorsulfonic acid at 35 C.The product was worked up as described in Example 3 and neutralized withsodium hydroxide solution to form a white, readily water-soluble paste.

Example 6 kgs. of ricinoleic alcohol were obtained by reduction ofricinoleic acid by means of sodium and amyl alcohol, adding water,separating the watery alkali hydroxide solution and removing the amylalcohol by distillation. The residue was treated with kgs. ofconcentrated sulfuric acid at a temperature between 10 and 20 C. Theproduct is worked up as described in Example 3 and neutralized by meansof equal parts of sodium hydroxide solution and potassium hydroxidesolution. An oily product readily soluble in water was obtained. Themain reaction is probably represented by the following equation:

Besides this reaction there may be also a reaction of only two or onlyone of the free groups (two hydroxyl groups and one double linkage)capable of reaction with sulfating means. These reactions yield forexample the following products:

CH3. (CH2) 5.CH.SO4H.CH2.CH=

CH. (CH2) 7.CH2.SO4H CH3. (CH2) 5.CHOH.CH2.CH=

CH. (CH2) 1.CH2.SO4H

Example 7 100 kgs. of stearic alcohol are treated at 40- 50 C. with 50kgs. of chlorsulfonic acid. The product is worked up as described inExample 3. A white paste is obtained. The reaction can be illustrated bythe following formulae:

Example 8 100 kgs. of a mixture of the alcohols obtained bysaponification of spermaceti oil by means of caustic lime anddistillation of the saponification product according to U. S. A. Patent1,290,- 870, said alcohols having an iodine number of about 50 andconsisting mainly of cetyl alcohol and oleic alcohol, are mixed with 100kgs. of concentrated sulfuric acid at 40 C. The mass is then poured into200 kgs. of ice water. The mixture is neutralized by adding sodiumhydroxide solution of 28 B.. The resulting solution containing 15-20%calculated on free fatty alcohol,

is introduced in a spraying drier of the Krause system and dried at atemperature between '75- 80 C. the temperature of the hot air enteringat the bottom of drier being about 170 C. Before or after the dryingoperation such quantities of Glaubers salt may be added to the solutionor to the dried product respectively, that the final product containsfor example 35% calculated on free fatty alcohol.

Example 9 100 kgs. of linoleic alcohol obtained by reduction of linoleicacid by means of an alkali metal and ethyl alcohol in a manner known perse, are dissolved in 50 kgs. of water free ethyl ether and treated with200 kgs. of concentrated sulfuric acid at a temperature between -5 C.for several hours. The product is mixed with 300 kgs. chopped ice and 50kgs. ethyl ether, washed with saturated Glaubers salt solution andneutralized by means of triethanolamine.

The reaction is probably represented by the following equation:

Besides the esterification of the CHzOH group addition of sulfuric orsulfonic acid to one or both of the double linkages may also occur.

The more volatile portion of the mixture of alcohols obtained fromcoconut oil as described in Example 1 may be removed therefrom bydistillation. The residue consists essentially of lauryl alcohol withsmaller portions of myristyl and higher alcohols and possibly traces ofdecyl and/or lower alcohols. Upon sulfonation of this mixture asdescribed in Example 1 or 2 and neutralization of the resultingderivatives with salts of sodium, potassium, ammonium, calcium, lithiumand/or magnesium, etc. detergents having very satisfactorycharacteristics are obtained. The sodium and other salts of thesederivatives have been found to be of particular value when substitutedfor or used in admixture with soap or soap-like products. For example,in scouring textiles of all types including wool, silk, cotton,regenerated cellulose or mixtures thereof; in the production of dyes andpigments and in the application of said dyes and pigments to textilematerials, to rubber and rubber-like substances, to plastics such asnatural and synthetic resins, etc.; in the concentration of latexwithout coagulation of the concentrated latex; in forming aqueousemulsions of mineral oils and derivatives thereof including asphalt,rubber or rubber-like substances. In carrying out the foregoingprocesses as well as the innumerable other procbsses suggested therebyor related thereto it is frequently desirable to incorporate freealcohols in the treatment. These alcohols may advisably correspond tothe ester or esters utilized or to homologues thereof, preferably butnot necessarily containing from eight to eighteen carbon atoms. Theproportion of such alcohols may vary from traces to many times theamount of esters present, and in some cases the described alcohols ormixtures thereof may practically be substituted for the esters,particularly when incorporating pigments or other solid materials intosubstances such as rubber, natural and synthetic resins, etc.

The following fatty materials have been found particularly suitable forconversion to alcohols and thence to sulfuric acid derivatives: tallow,

lard, whale oil, coconut oil, palm kernel oil, Palm oil, olive oil,castor oil, linseed oil, tall oil, technical stearic acid, technicaloleic acid and ricinoleic acid, palmitic acid, tallow fatty acids, Japanwax, spermaceti, sperm oil, herring oil, beeswax, montan wax, methyl,ethyl, propyl and butyl esters of technical fatty acid mixtures such asstearic acids, oleic acids, tallow fatty acids, linseed oil fatty acidsand whale oil fatty acids.

Alcohols coming within the scope of this invention are, as previouslymentioned, advantageously sulfated with concentrated or fuming sulfuricacid or chlorsulfonic acid and at reduced temperatures within the rangeof 0-30 C. or at temperatures wherein the alcohols are present in theliquid phase. This treatment may be carried out in the presence oforganic solvents or diluents and likewise in the presence ofwaterbinding agents such as acid anhydrides or anhydrous acids, forinstance acetic anhydride, phthalic anhydride and sulfur trioxide.

Prior to or simultaneously with the aforementioned sulfation treatmentthe alcohols or mixtures thereof may be treated with other reagents ofan acidic nature. Such reagents may be of organic or inorganic origin,for example, boric, phosphoric, acetic, sulfurous, hydrochloric,hydrobromic, nitrous, nitric, propionic, butyric, benzoic, phthalic,sulfanilic, naphthionic and/or related acids or derivatives thereofwhich have an acid character. The amounts of such acids or derivativesthereof including their anhydrides which are used may vary widelydepending upon the alcohols treated, the strength of the reagents andthe objects in view. Treatment with the aforementioned substances ispreferably carried out prior to treatment with the sulfating medium butmay also be carried out simultaneously with such sulfation treatment, oreven subsequent thereto if the sulfation treatment is of a relativelymild nature.

Where the alcohol is of an unsaturated nature the aforementionedtreatment is of particular value. As illustrative of this principal,oleyl alcohol or mixtures thereof with saturated and/or unsaturatedalcohols, particularly with alcohols previously described herein, mayfirst be treated with acetic acid or its anhydride. The resultingacetylated product may then be treated with chlorsulfonic acid. Theproducts of this combined treatment are probably mixtures of oleylalcohol derivatives containing one or more sulfate groups which in somemolecules are partially replaced by acetate groups, and also by a smallproportion of sulfonate groups. The particular type of product will ingreat measure depend upon the intensity of the sulfation treatment.Regardless of the heterogeneous reactions which take place the productis of pronounced value because of its detergent, wetting out andemulsifying properties. It is excellent adapted for the 4 usespreviously described, either alone or in admixture with other detergent,wetting out and emulsifying agents, including those described herein.

It may here be mentioned that the described alcohols esterified withinorganic or organic acids or substances of acidic nature but untreatedwith sulfating agents in many cases possess detergent, wetting out,stabilizing and emulsifying properties of their own and may be used assuch without subjection to sulfation treatment or may be used inadmixture with such products after sulfation treatment and/or inadmixture with alcohols which have been esterified solely with sulfatingagents.

The esterified products comprised within the scope of the presentinvention are advisably neutralized with inorganic or organicsalt-forming compounds, and preferably those salts or bases which formwater-soluble derivatives therewith. Compounds which are representativeof this category are soda ash, caustic soda, ammonium hydroxide, lithiumchloride, magnesium chloride, pyridine, piperidine, diethanolamine,triethanolamine, mono-methylamine, dimethylamine, cyclohexylamine,monoand diallwl-cyclohexyL amine, etc.

The aforementioned products, particularly the esterified higher normalprimary alcohol and preferably the water-soluble salts of sulfate estersof normal primary alcohols containing from twelve to eighteen carbonatoms are of distinct utility in the detergent, emulsifying, wetting outand frothing field. They are well adapted for use in the variousprocesses wherein soap or soaplike substances have been used in thepast. These new compounds may be used alone and/or in admixture withother compounds described herein and/or in admixture with soap orsoaplike substances and including the various assistants which haveheretofore been used to enhance the properties of soap or soap-likesubstances. In other words, wherever it was known to use soap orsoap-like substances in the prior art it is to be understood that partor all of said substances might be replaced by the previously describedcompounds. Examples of a few uses suggested thereby are: in the leatherindustry as in the dyeing, tanning, treating and other processing ofleather; in the textile industry, as in the washing of cotton, wool,silk, regenerated cellulose and other natural and synthetic materials aswell as combinations thereof,

in the weighting of wool or other substances having an afiinitytherefor, in the production of pigments and dyes and in theirapplication to textile or other material; in the manufacture ortreatment of soups, cosmetics, tooth pastes and powders, salves, creams,boring oils, coating materials, stencils, inks, dust-binding agents,insecticides, medicinal and other emulsions, polishes, waxes,foodstuffs, lubricating media, insulating media, paints, varnishes,lacquers, plastic compositions, latex, synthetic and natural rubberproducts and perfumes.

As a general rule it may be stated that for detergent, emulsifying,wetting out and frothing purposes water-soluble salts of sulfate estersof normal primary alcohols having from twelve to eighteen carbon atomsare preferred. Derivatives of lower or higher molecular weight alcoholsmay also be used although they are ordinarily not so eificacious. Thepresence of corresponding free alcohols or their homologues isfrequently advantageous for this purpose. Where an intimate mixture ofnon-analogous solids is desired the higher fatty alcohols may advisablybe used alone or in conjunction with the aforementioned esters or theirpreviously described derivatives.

The present invention is in part disclosed in my prior applicationsSerial Nos. 350,135, filed March 26, 1929, now Patent No. 1,968,793;382,078, filed July 29, 1929, now abandoned after transferring itssubject matter and claims to the Application Serial No. 448,806;433,815, filed March 6, 1930, now Patent No. 1,968,794; 448,806, filedApril 30, 1930, now Patent No. 1,968,795; and 650,203, filed January .4,1933, now Patent No. 1,968,797, of which the present application is acontinuation in part.

As many apparently widely different embodiments of this invention may bemade without departing from the spirit and scope thereof, it is to beunderstood that the invention is not limited to the specific embodimentsthereof except as defined in the appended claims.

I claim:

1. Compounds having the following general formula:

wherein R is an open chain hydrocarbon radical containing at least eightcarbon atoms, X is an acid group other than CO0H, Y is a sulfate group,and n is an integer.

2. The compounds described in claim 1 characterized in that the groupdefined by X is of inorganic origin.

3. The compounds described in claim 1 characterized in that the groupdefined by X is of organic origin.

4. The compounds described in claim 1 characterized in that the groupdefined by X is a member selected from the class consisting of borate,phosphate, acetate, sulfonate, chloride, bromide, nitrite, nitrate,propionate, butyrate, benzoate, phthalate, phenylamino-sulfonate, andnaphthionate, groups.

5. Wetting, detergent and emulsifying agents characterized in that thecarboxyl group of fatty acid esters having more than 8 carbon atoms inthe acid radical is changed to a methylene sulfonate group, and furthercharacterized in that additional groups of an acidic nature aresubstituted thereon.

6. Wetting, detergent, and emulsifying agents characterized in that thecarboxyl group of fatty acid esters having more than 8 carbon atoms inthe acid radical is changed to a methylene sulfate group, and furthercharacterized in that additional groups of an acidic nature aresubstituted thereon.

7. Wetting, detergent and emulsifying agents characterized in that thecarboxyl group of fatty acid esters having more than 8 carbon atoms inthe acid radical is changed to a CH2SO3H group, and furthercharacterized in that additional groups of an acidic nature aresubstituted thereon.

8. In the production of compounds suitable as wetting, detergent andemulsifying agents, the steps which comprise catalytically hydrogenatinga fatty material to form a higher molecular alcohol corresponding to afatty acid radical of said fatty material, introducing into the moleculewith the higher molecular alkyl radical of said alcohol a polybasic acidradical whereby a compound is formed having oil solubilizingcharacteristics imparted by the higher molecular alkyl radical and watersolubility by the acid radical.

9. In the production of compounds suitable as wetting, detergent andemulsifying agents, the

steps which comprise subjecting a fatty material to catalytichydrogenation at an elevated temperature and pressure, thereby forming ahigher molecular alcohol, and introducing into the molecule with thehigher molecular alkyl radical a sulfonate radical whereby a compound isformed having oil solubilizing characteristics imparted thereto by thehigher molecular alkyl group and water solubility by the sulfonatradical.

10. A wetting. detergent and emulsifying agent composed 01' a mixture ofcompounds having oil solubilizing characteristics imparted thereto byhigher molecular alkyl radicals and water solubility by sulfonategroups, said higher molecular aikyl radicals being obtained throughcatalytic hydrogenation oi a fatty material.

11. A composition oi matter having wetting, cleaning and emulsifyingproperties consisting of sulfonated compounds tree of carboxyl radicals,which compounds have higher molecular alkyl radicals imparting oilsolubllizing properties and neutralized sulionate groups which impartwater solubility, said higher molecular alkyl radicals being those ofhigher molecular alcohols obtained by the elevated temperature andpressure catalytic hydrogenation of a fatty material.

HEINRICH BERTSCH.

